Gotta love that windows hate, seriously. Both OS's have issues. How many times has a upgrade of OSx corrupted Capture One1? It always amazes me how polarized the OS issue can become. I use both and each have issues, but somehow in 20 years of use, I can make it. NET, if you like the layout of the Surface product, don't let the OS get in the way.
Back to the Surface.
I have used them since the pro 2. Hear are a few thoughts from a user.
1. Only 1 USB3 port, had hoped this would grow to 2 in the Surface 4, and that port still seems to have limited power. It will tether a IQ Back. I also don't believe even the S4 has USB 3.1.
2. The Surface 3 was hard to read with apps like C1 or LR as Adobe/Microsoft did not allow the screen to adapt for reading, like Mac/retina does. Net, you would have a real hard time reading a retina on a 13 inch at full res. Adobe only gives you a 200% step on the Surface 3 and that's too much it needs to be 150%.
3. The Surface 4 has a slightly larger screen and I did not find as much an issue when using Adobe apps or C1
4. The i7 on the S3 was a battery hog and got hot pretty quick. I have the i5 and it can go about 2.5 hours when tethering in the field. (note the S2 is the king for battery life easily getting 3.5 hours of actual use.
5. The keyboard is extra and around 100.00, which to me should be just included in the price
6. The S4 comes with win10 and it's an overal much better version of windows than 8.1.
7. All of the screens become a mirror in outdoor light, just like a Macbook retina. So tethering in bright light is tricky but can be done
8. If you go S4 I recommend a 2nd pen as when working on the screen with apps finger touch can be a bit tricky with big fingers. It's easy to drop and loose the pen.
As for lockups, etc. Really I have found the Surface line to be very strong. I purchased late in the life of the 2 and it's been solid. Dropped it 2x, once on payment, and it's still going strong. Purchased the 3 early and no doubt Microsoft was still tweaking that machine. I ended up getting a full replacement as mine did run very hot. The 2nd unit is not 1.5 years old and has not had any issues. I did upgrade to win 10 on it. Prefer it to 8.1. Have LR, CC, and C1 9 on it currently. Make sure to get 8GB of ram and 256GB hard drive if you are going to do a lot of work on it. The keyboards on the 3 and now 4 work fine, and were a huge improvement on the S2 keyboard, which did suck.
You can read a lot about tethering solutions for the Surface here:
https://kendoophotography.wordpress.com/2015/05/29/tethering-with-the-surface-pro-evolving-clamp-choices/Ken has done a ton of work on this. The last solution with the magnets is what I use and love it.
The main issue on the Macbook, is the dedicated keyboard. If you are in studio only, simple solution. If you are going to carry in the field, the S4, with a keyboard that can bee totally removed is hard to beat, at least to me.
Paul C